Triethylamine → Triethylsilane

HRID 1420797Notes

Reaction equation

HRID 1420797 reaction equation
C(OC(=O)N[CH2:11][CH:12]1[CH2:17][CH:16]2[CH2:18][CH:14]([C:15]2([CH3:20])[CH3:19])[C:13]1=[CH2:21])C1C=CC=CC=1.[CH2:23]([SiH:25]([CH2:28][CH3:29])[CH2:26][CH3:27])[CH3:24].[CH2:30]([N:32](CC)CC)C>C(Cl)Cl.[Pd](Cl)Cl>[CH3:20][C:15]1([CH3:19])[CH:14]2[CH2:18][CH:16]1[CH2:17][CH:12]([CH2:11][CH2:30][NH2:32])[C:13]2=[CH2:21].[CH2:23]([SiH:25]([CH2:28][CH3:29])[CH2:26][CH3:27])[CH3:24]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 12052TriethylsilaneHCID 54031778(6,6-Dimethyl-2-methylene-bicyclo[3.1.1]hept-3-ylmethyl)-carbamic acid benzyl ester

Product 2

HCID 12052TriethylsilaneHCID 18782837C-(6,6-Dimethyl-2-methylene-bicyclo[3.1.1]hept-3-ylmethyl)-methylamine

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

(6,6-Dimethyl-2-methylene-bicyclo[3.1.1]hept-3-ylmethyl)-carbamic acid benzyl ester (988 mg, 3.30 mmol) was dissolved in CH2Cl2 (20 ml) under an atmosphere of dry N2. To this solution was added triethylsilane (2.10 ml, 13.2 mmol), triethylamine (330 μl, 2.37 mmol) and palladium(II) chloride (165 mg). The reaction was then heated to reflux and stirred at this temperature for one hour. The reaction was then quenched with the addition of saturated ammonium chloride solution (3.0 ml). The reaction is then partitioned between CH2Cl2 and 0.1 N NaOH. The CH2Cl2 layer was dried over MgSO4, filtered and concentrated under vacuum to give the titled compound along with unreacted triethylsilane: C.I. m/z 166 [M+1].

Workup

  1. temperatureThe reaction was then heated
  2. temperatureto reflux
  3. customThe reaction was then quenched with the addition of saturated ammonium chloride solution (3.0 ml)
  4. customThe reaction is then partitioned between CH2Cl2 and 0.1 N NaOH
  5. dry with materialThe CH2Cl2 layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-8645d326b3bc446fbbcaae81fd254b4c
Source dataset
uspto-grants-2000_06
Patent number
US06071935

Reaction notes

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